First determine the strength of the cigar. Generally as a rule, the darker the wrapper, the stronger the cigar will be. Every cigar, being hand-made, has a distinct taste. Cigar strengths are divided into 3 main categories: mild, medium-bodied, and strong. There are also cigars that fall between the 3 categories.
Next, look at the wrapper leaf. It should have a mild sheen and feel smooth. It should not be heavily veined. The various colors of the wrappers are candela (greenish), natural (light brown), Colorado or Rosado (reddish brown), Habano (darker brown), Maduro (dark brown) and Oscuro (dark brown bordering black). The different types of tobacco leaves change their colors based on how they are grown. When the tobacco is grown in direct sunlight, they are darker. While when grown in the shade, they are lighter.
After looking the wrapper over, feel the cigar to make sure that it does not have soft spots and that it is evenly rolled. It should feel firm but not overly tight. Soft spots cause the cigar to burn hot and uneven. While too tight makes the draw very difficult.
Determining how much time you have to smoke the cigar also determines the length of it. Cigars are measured by inches in length and by ring size in width. 1 ring size is equal to 1/64 of an inch. The larger the ring size, the slower, cooler burning the cigar will be. Wider cigars (those with larger ring sizes) have more tobacco in them and tend to have more complex and delicious flavors than small ring size cigars.
After you have selected the ideal cigar for you, try others in order to broaden your cigar horizon. You’ll find that based on many factors, time of the day, your mood, changing tastes, etc…, you will smoke different cigars with different flavors.